Oliver's problem
by Stuckfan
Summary: Oliver turns to Taylor for some sisterly advice.


Story requested by Ks1999

I'm trying to do homework. I hate math, I'm not going to need it. I'll just get by on my looks and sport skills. I know, I should, be like, a better woman or something, but eff that. I know I'm hot and I don't mind using it. Trip sure doesn't mind. The way he used this body of mine last night, yeah he doesn't mind at all.

Mom and Dad are with Annalist at some school event and Oliver should be in his room practicing his ballet. I start thinking about all the things Trip and I did last night. It isn't like it was our first time or anything, but damn was it good. I run my hand down my body, feeling the curve of my breast, my flat stomach, and finally Trip's favorite place, my pussy. Damn clothes are in the way. I unbutton my shorts and reach inside. I'm already soaked myself thinking about yesterday, so when my fingers connect with my clit. Wow I almost cum right now. I start to play with myself, small circles at first. Teasing.

"Hey Taylor" I hear as my door opens and Oliver walks in.

"Fuck" I yell as I try to pull my hand out, but it is too late he saw what I was doing. "Sorry" he says as I yell louder, " Knock first asshole"

He apologies over and over again, to the point that it sinks in and I know he really did make a honest mistake. "Look Oliver, It's ok. I forgive you. Now why did you come in?"

I'll admit If it weren't for this whole learning to be a better person think I'm trying, I would have already kicked him out and trashed him on my social media. I sit back and listen to his story about wanting fulfill a fantasy for his girlfriend. I congratulate him on being a good boyfriend, but then he tells me what she wants. I have to admit shocked is a small word to describe my feelings.

I believe what she wants is called pegging. If you don't know the term, let me educate you. She wants to but on a strap on and fuck Oliver in his ass. From what I've heard, it can be fun for the guy, as long as he is relaxed enough. I mean when I let Trip in the backdoor I know I can't tense up or I'll have no fun at all. I have to assume that works for guys as well. Damn it I need to get a gay guy friend. I could compare notes.

I can't believe his vanilla girlfriend wants this. I ask him, how he feels about all this. "That's what I can in here for. I want to make her happy, but I don't know if I could do this. I already had everyone thinking I'm gay before. What if people find out I'm ok to do this? No one would think I'm not gay."

I look at him, he isn't homophobic, but he always worries what people think about him. He thinks it could affect how much money he will make in the future. "So you want to do this? Not just because she asked. You would be willing even if it weren't her?" He thinks about it. Really thinks. Wow, we are having a real conversation. That hasn't happened in a long while. "Yes, I'll admit. I never thought about it before. But now I think I would want to try it one day. Even if it isn't with her. "

"Ok, so the next question. Do you trust her enough or do you want to wait until you find someone else?"

"I think I'll wait, but now that this is in my head. Well I want to try it"

I laugh, and tell him. You want it, go get that girl of his. He laughs and goes to leave when he stops. "Wait, you could help me"

I look at him confused, " You want me to ask your girlfriend for me?" "No" He corrects me "I you could do it to me."

"What! I'm your sister!"

"That's why it's perfect. I know you are not going to go telling everyone. This would be our secret. I know you and Trip are involved, so you are not going to freak out about seeing a penis. I know you have a strap on, because I helped you clean this pig pen of a room. Why do you have that anyway?"

I explain how I won it at a party, meanwhile I'm trying to come to terms with what he is asking. He wants me to fuck him. I guess I wouldn't really have to do much. A little lube and some hip action. Might even be a bit fun. I could see what sex is like from Trip's perspective. Oliver must know I need sometime to think about it, because he isn't pressuring me or anything. We just chat about whatever, while everything is going through my mind.

"If I do this..." I start " we need to set up some ground rules"

"Of course Taylor, what did you have in mind?" his quick agreement lets me know how much he really wants this.

We talk, of course no one can find out about this. I doubt Trip will understand what is about to happen. Then Oliver makes a request of him own. "I don't want to just get fucked. I want to fuck as well. I can't just lay there, I would like this to a be a two-way street, and I promise I would do more than you are doing for me. I will do more than just use you."

"Oh Oliver, Trip doesn't just use me. I use him."

"I know, Taylor, but that doesn't mean you can't have more. Let me treat you like the sexy woman you are."

I think about his words. I don't have a problem with my sex life, however he is talking about intimacy. Trip and I have that, as least as much as you can have with a man like Trip. I wonder what Oliver could do for me. Would do to me. "Ok, I'm willing to try"

I don't know if I expected the kiss or not, but Oliver leaned in. His lips were soft and caring on my mine. His hand caressed my face as he pulled me to him. It was already very different from any guy I've been with. They are always kissing me as a prelude to touching, revealing something else. Oliver was right here, right now. It doesn't feel rushed. It feels loving.

As we kiss, Oliver has lowered himself to the bed and pulled me on top. While I have made out like this, this still feels different. Like I'm in control and that makes me powerful. I run my hands up and down his chest. All that ballet practice has turned him into a strong man. I can feel his bulge against me. Good sign. I move my lips to his neck, I feel his against mine. He is a good kisser. Brie is a lucky girl. His hands are roaming my back, feeling the contours of my body. I sit up and remove my shirt, I'm so lucky I decided to wear one of my good bras.

Oliver takes a second to look at my breast. He smiles, as he sits up and kisses the area between them. Again I wasn't expecting it. All guys go for one or the other, left or right. "Oh Oliver" I moan into his ear. I reach behind myself and unhook the bra. I find one of Oliver's hands on my left breast, his fingers playing with the nipple and his mouth on the other one. He doesn't suck on it, but kisses my nipple. Opens his lips and I feel his lounge circle it, flick it, pay attention to me in a way no one has. Oliver wasn't joking, he is treating me better than any other guy has. I don't think Trip is treating me badly or anything, but we fuck and this, this is something else.

"Oliver, don't ever stop"

It seems, at some point, he decides I need something else. I help him remove his shirt and pants. I also remove my own. We both look each other over, the tent in his underwear promises a good fit. The dampness in my panties show how much I am enjoying this. I lean in and kiss him. I try to show him how much this means to me. How he is opening my eyes to what can be. He holds me close and pulls back, " Taylor, you are so beautiful. Thank you for helping me and for allowing this."

We kiss again as he pulls my panties off. I open my legs slightly, allowing him whatever he has planned. I reach for his manhood and get my first real feel for what he is working. Good size and girth. I hope Brie appreciates what she has. I rub him as I feel his first touch of my womanhood. He doesn't rush to finger me or try to feel every inch at the same time. No, it is like he is touching something fragile. He is careful not to break it, but still wants to experience everything. I am on fire. How can someone be doing so little yet so much? "Oliver, you are doing things I didn't know were possible."

I reach into his briefs and wrap my hand around his member. I get a feel for him as his fingers continue to explore me. I move my hand a bit, I want to know what he likes. I use his reactions and react accordingly. Oliver starts to kiss my body again, at least I know what he is going to do this time. As he kisses his way down, I feel confident I finally know what Oliver's goal is. As his lips touch my wetness I moan. I can no longer reach him, so I play with my tits as Oliver does his special magic. "Oliver, yes...yes." When I cum, it isn't slow or unplanned, no it is everything and all at once. An explosion, a bomb, all light and joy.

I come back to myself to find Oliver next to me. He watches as I calm down and waits. I lean over and give him a quick peck. "Thank you" He smiles and I push him down. I don't have the moves he has. I lower my head to his shaft. I take it into my hand and open wide. I give it all I have, use every trick I know. "Taylor, damn you are good" I smile to myself. As least, it won't be all him. I have something to give back. I started to worry. I take him in as much as I can. His cock head hitting the back of my throat, over and over. I should be gagging, but I have never been more motivated to give it my all before. I resist the urge and hope to be rewarded with his seed running down my throat. "FUCK TAYLOR" He yells as he releases his sauce. Tasty.

I look up at him as I swallow. He laughs, not a mean laugh, just the chuckle of a guy who knows what I just did. I smile and rejoin him on the bed. We talk for a bit before I bring up what we both must be thinking. "Do you still want to try it?" He leans over and gives me a small kiss. "Yes"

I stand and go to my drawer, I pull out my strap on and a small bottle of lube. I put the toy on and join him on the bed. I ask, "How do you want this?" He lays down and opens his legs. I squirt a generous portion into his anus and on my hand. I use my fingers to lube him and the toy up. I finger him for a little as well. Hoping to get him use to what I'm about to do. His cock has regrown, so I use my other hand and jerk him off. "Are you ready?" He shakes his head and I place to tip of the toy against him.

I move slowly, first an inch. Then another. "Taylor, it feels better than expected." Encouraged I move forward again. Before long the whole 10 inches are inside my brother. He takes it well, better than I ever have. I start to fuck him slowly, he tells me to go faster. I comply. As my hips go back and forth my tits are bouncing. I start to wish I had a mirror or set up my phone to record this. I want to know what I look like, somehow I think it must be hot. "Taylor, fuck yes" Oliver interrupts my thoughts. I go back to jerking him off. His cock standing straight and tall thoughtout this process.

I reach down, shit I'm soaked. Who knew fucking your brother could be such a turn on. I wonder if this could happen again. We agreed to a one time thing, but damn. I would be willing for more. I wonder if I can get Oliver to teach Trip how to be a better lover. I would do a lot for him in return. Maybe Brie would be up for a threesome. "Taylor, fuck me" he commands.

I move faster and use both my hands on his cock. "Take this dick" I try my hand at dirty talk. He gives me a look that says, no. I shut up and push harder. He grunts but smiles. I wink at him and hope he cums soon. I want to talk with him. I notice his balls jump up and then my hands are covered. "YES! " he yells. I move slowly and pull the toy out. I go to clean up and toss him a towel to do the same.

I go back to the bed and lay down next to him. "Thank you, Taylor" he says after a quick kiss. "Your welcome, this was so much fun"


End file.
